| Perfuming ingredients capable of imparting woody odors -> Monitor Keywords |
|
|
Perfuming ingredients capable of imparting woody odorsRelated Patent Categories: Perfume Compositions, Perfume Compositions, Oxygen Containing Active IngredientPerfuming ingredients capable of imparting woody odors description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20060241014, Perfuming ingredients capable of imparting woody odors. Brief Patent Description - Full Patent Description - Patent Application Claims
CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation of International application PCT/IB2004/003981 filed Nov. 30, 2004, the entire content of which is expressly incorporated herein by reference thereto. TECHNICAL FIELD [0002] The present invention relates to the field of perfumery. More particularly, it concerns a 1,8a-methano-2,4a,8,8-tetramethyldecahydro-2,3-naphthalenediol derivative of formula (I), as defined below, and its use as perfuming ingredient. BACKGROUND [0003] To the best of our knowledge, only two compounds of formula (I) are known from the prior art. Said compounds are the 3-acetate of [1aR-(1a.alpha.,2.beta.,3.beta.,4a.beta.,8aS)]-decahydro-2,4a,8,8-tetrame- thyl-cyclopropa[d]naphthalene-2,3-diol, and the 2-acetate of (1aR,2S,3S,4aS,8aS)-decahydro-2,4a,8,8-tetramethyl-cyclopropa[d]naphthale- ne-2,3-diol which are reported as intermediate compounds in the oxidation of thujopsene (e.g. see G. Ohloff et al. in Helv. Chem. Acta 1970, 623 or G. Ohloff et al. in Recueil des Travaux Chimiques des Pays-Bas, 1974, 93, 264). However, none of the prior art documents mentions or suggests that said compounds can be used as perfuming ingredients. The other compounds of formula (I) are new. [0004] The closest analog, which is reported in the prior art as a perfuming ingredient, is 4,7,11,11-tetramethyl-tricyclo[5.4.0.0(1,3)]undecan-5-one disclosed in U.S. Pat. No. 3,839,232. Said document does not suggest that the compounds of the present invention are also useful perfuming ingredients. SUMMARY OF THE INVENTION [0005] The present invention now relates about the derivatives of 1,8a-methano-2,4a,8,8-tetramethyldecahydro-2,3-naphthalenediol, of formula (I) as defined below, their use as perfuming ingredient, as well as the perfuming compositions or articles associated with such compounds. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS [0006] Surprisingly, we have now established that the 1,8a-methano-2,4a,8,8-tetramethyl-decahydro-2,3-naphthalenediol derivative of formula wherein R.sup.1 or R.sup.2, taken separately, represents each a C.sub.1-3 alkyl group or a COR.sup.3 group, R.sup.3 representing a methyl or ethyl group, and one of said R.sup.1 or R.sup.2 may also represent a hydrogen atom; or said R.sup.1 and R.sup.2, taken together, represent a C(R.sup.4).sub.2 group, each R.sup.4 representing a hydrogen atom, a C.sub.1-3 alkyl group or, taken together, a CH.sub.2--(CH.sub.2).sub.2--CH.sub.2 or CH.sub.2--(CH.sub.2).sub.3--CH.sub.2 group; in the form of any one of its isomers or of a mixture thereof, possesses a very useful woody-ambery type fragrance, which renders them very convenient for the preparation of perfuming compositions and perfumed products. [0007] According to a particular embodiment of the invention, R.sup.1 or R.sup.2, taken separately, represents each a C.sub.1-3 alkyl group and one of said R.sup.1 or R.sup.2 may also represent a hydrogen atom, or said R.sup.1 and R.sup.2, taken together, represent a C(R.sup.4).sub.2 group, each R.sup.4 representing a hydrogen atom or a C.sub.1-3 alkyl group or, taken together, a CH.sub.2--(CH.sub.2).sub.2--CH.sub.2 or CH.sub.2--(CH.sub.2).sub.3--CH.sub.2 group. [0008] A preferred compound of the invention is the (1R,4aS,8aS)-1,8a-methano-2,4a,8,8-tetramethyldecahydro-2,3-naphthalenedi- ol derivative of formula wherein each R.sup.4 represents, independently from the other, a hydrogen atom or a C.sub.1-3 alkyl group, preferably a methyl group. As previously, compound of formula (I) may also be in the form of any one of its isomers or in the form of a mixture of said isomer. [0009] A typical example of the invention's compounds is (1R,4aS,8aS)-2,3-(dimethylmethylenedioxy)-1,8a-methano-2,4a,8,8-tetrameth- yldecahydronaphthalene, the odor of which being characterized by a substantive woody-ambery character, which is in the same direction of the one of 1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol but is less dry, more cedar and sweeter. Moreover the odor of said invention's compound is also characterized by the presence of floral-red fruit notes, which are very surprising for a compound belonging to the woody-ambery olfactive family. Said floral-fruity notes can contribute in a very positive and non-conventional manner to the odor of the accords, perfumes, into which the invention compound is added. [0010] Another example of compound (II) is (1R,2R,3S,4aS,8aS)-2,3-(dimethylmethylenedioxy)-1,8a-methano-2,4a,8,8-tet- ramethyldecahydronaphthalene which has an odor very close to the one of the (1R,4aS,8aS) isomer, mentioned above, but which shows an additional "lait de santal" note. Said (1R,2R,3S,4aS,8aS) isomer imparts a very similar odor, but having a stronger intensity, when compared with its diastereomer of configuration (1R,2S,3R,4aS,8aS). [0011] The invention's compounds can be easily prepared by oxidation of thujopsene into the corresponding diol, e.g. by standard means such as OSO.sub.4. The diol thus obtained is subsequently transformed into the invention's acetal, ester or ether according to any standard procedure for such chemical transformation. A specific example is provided in the Examples. [0012] Due to the surprising properties of the compounds of formula (I), another object of the present invention is a perfuming composition comprising [0013] i) at least one invention's compound as defined above; [0014] ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and [0015] iii) optionally at least one perfumery adjuvant. [0016] By "perfumery carrier" we mean here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients. Said carrier may be a liquid or a solid. [0017] As liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting examples solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used. [0018] As solid carrier one may cite, as non-limiting examples, absorbing gums or polymers, or yet an encapsulating materials. The encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation techniques. [0019] Generally speaking, by "perfumery base" we mean here a composition comprising at least one perfuming co-ingredient. [0020] Said perfuming co-ingredient is not of the formula (I). Moreover, by "perfuming co-ingredient" it is meant here a compound, which is used in perfuming preparation or composition to impart a hedonic effect. In other words such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. [0021] The nature and type of the perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds. [0022] For the compositions which comprise both a perfumery carrier and a perfumery base, then other suitable perfumery carrier, than those previously specified, can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark ISOPAR.RTM. (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark DOWANOL.RTM. (origin: Dow Chemical Company). Continue reading about Perfuming ingredients capable of imparting woody odors... Full patent description for Perfuming ingredients capable of imparting woody odors Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this Perfuming ingredients capable of imparting woody odors patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored. 3. Each week you receive an email with patent applications related to your keywords. Start now! - Receive info on patent apps like Perfuming ingredients capable of imparting woody odors or other areas of interest. ### Previous Patent Application: Improved liquid fabric softener Next Patent Application: Cancer genes Industry Class: Perfume compositions ### FreshPatents.com Support Thank you for viewing the Perfuming ingredients capable of imparting woody odors patent info. IP-related news and info Results in 0.24026 seconds Other interesting Feshpatents.com categories: Canon USA , Celera Genomics , Cephalon, Inc. , Cingular Wireless , Clorox , Colgate-Palmolive , Corning , Cymer , 174 |
 * Protect your Inventions * US Patent Office filing 
PATENT INFO |
|
